Conversations You Aren’t Ready to Hear: The Self-Reflection of Leadership

Even CEOs need to ask: If I were my own boss, would I fire me?

Leadership is messy. It’s not just about giving orders or closing deals, it’s about showing up honestly, owning your habits, and building a place people want to work. As a small business owner, you’re both boss and team member, vision-carrier and culture-keeper. The question you’ve been avoiding: If you were your own boss, would you keep you on the team?

In this post, we’ll dig into why leadership self-reflection is crucial, what it looks like in practice, and how you can start doing it today.

Why Self-Reflection Isn’t Optional Anymore

Research from Gallup shows that just 32% of U.S. employees feel engaged at work. One major reason? Leadership. Only 19% of employees say they’re “extremely satisfied” with their workplace as a place to work.

When leadership doesn’t reflect, align, or listen, culture suffers, which in turn affects retention, performance, and brand. In fact, 42% of voluntary employee turnover is preventable yet ignored by management.

For Florida small-business owners (or anywhere really), that means your leadership style and self-awareness aren’t just “nice to have” , they’re competitive differentiators.

1. If You Were Your Own Boss… Would You Fire You?

This isn’t about self-loathing. It’s about honest audit. Ask yourself:

• Am I modeling the behavior I ask of my team?

• Do I meet the standards I set?

• Do I hold myself accountable when things go sideways?

  
  

Why it’s important

Leaders set the tone. If your behavior says “delegate everything” while your team sees you micromanage, you’re sending mixed signals. Good leadership alignment reduces ambiguity and improves trust.

Tip for small business owners

Set aside 30 minutes this week with a notepad (no phone) and answer:

“If someone applied to be my boss, would I hire me for this role?” Write your answer, then identify two habits you need to change.

2. Ego ≠ Leadership, Accountability Does

Ego drives decisions from “me first.” Leadership asks “what’s best for the people we serve?” In today’s changing workplace, clarity, humility, and transparency matter more than ever. Gallup’s research shows that when employees strongly agree they trust leadership and leadership communicates well, they are 4.5 times more likely to be engaged.

Practical actions

• Have a “fail forward” conversation with your team: What didn’t go well this quarter and what did we learn?

• Ask your team: “What’s one thing I could do as a leader that would make your job easier?”

• Track responses from your team in a simple leadership journal or tracker then review monthly.

  
  

3. Build Reflection Into Your Routine

Reflection isn’t a one-and-done. It’s a rhythm. Without it, even the best intentioned leaders drift.

Quick routine for you

• Weekly 10-minute check-in: “What went well?” “What would I redo?”

• Monthly team pulse: Use a simple survey (“What support do you need from me?”) and discuss in a one-on-one.

• Quarterly growth goal: Choose one leadership behavior (e.g., delegation, feedback frequency) to improve. These routines keep you aligned, visible, and approachable, key traits in high-performing small teams.

  
  

4. Self-Awareness = Retention Strategy

It’s not just about keeping people—it’s about keeping the right people. One key reason employees leave? Leadership and culture issues. Gallup found that 75% of employees left because of their manager or leadership.

For small businesses in Florida, that means your reputation travels fast. A leader who listens, adapts, and models growth builds culture, and culture keeps people.

At your next team meeting, say:

“Here’s one thing I’m working to do better as your leader… I’d love your feedback in three weeks to see if you’ve noticed a difference.” This small gesture signals you’re open, accountable, and evolving.

Leadership Self-Check Exercise

Question	Your Rating (1–5)	Action to Take
I model the values I ask my team to live.
I invite feedback about me as a leader.
I track one leadership behavior each quarter.
My team would say I listen more than I talk.
I close the loop on feedback and update the team.

Pick your lowest-rated question. Create one action step this week and one follow-up check for next month.

Leading a small business doesn’t mean you have to carry everything on your own, but you do need to lead yourself first. Because when you reflect, adapt, and show up with humility, your team does too. When leadership gets real, culture becomes your advantage, not your afterthought.

So this week: ask the hard question, set the check-in, and commit to being the leader worth following. Your business (and your team) will thank you for it.